TY - JOUR
T1 - Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines
AU - Clayden, Jonathan
AU - Lai, Lai Wah
AU - Helliwell, Madeleine
PY - 2004/5/10
Y1 - 2004/5/10
N2 - Condensation of atropisomeric tertiary 2-formyl naphthamides or 2-formyl benzamides with some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched form. Evidence that the reactions are under thermodynamic control is presented.
AB - Condensation of atropisomeric tertiary 2-formyl naphthamides or 2-formyl benzamides with some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched form. Evidence that the reactions are under thermodynamic control is presented.
KW - Atropisomeric amides
KW - Ephedrine
KW - Imidazolines
KW - Oxazolidines
UR - http://www.scopus.com/inward/record.url?scp=1942436911&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2004.01.101
DO - 10.1016/j.tet.2004.01.101
M3 - Article (Academic Journal)
AN - SCOPUS:1942436911
SN - 0040-4020
VL - 60
SP - 4399
EP - 4412
JO - Tetrahedron
JF - Tetrahedron
IS - 20
ER -